


Pleasant Surprises

by holloway88



Category: Critical Role (Web Series)
Genre: Anal Fingering, Anal Sex, Butt Plugs, Caleb is soft, Essek is a pillow prince, Library Sex, M/M, Magic, inappropriate use of magic
Language: English
Status: Completed
Published: 2019-08-12
Updated: 2019-08-12
Packaged: 2020-08-20 02:04:18
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,860
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20219986
Author URL: https://archiveofourown.org/users/holloway88/pseuds/holloway88
Summary: “Am I boring you, Thelyss?” he asked, cheeks a little rosy from the heat of the candles that melted beside him, droplets of wax spilling onto the desk.“You could never bore me, Widogast.” Essek grinned and straightened himself out. He had lost the robe and mantle hours before, it hung elegantly off to the side of the room, and his tunic was unfastened at the top. “I was merely admiring you.”Essek and Caleb are studying arcane thesis papers and decide to take a break to rest their eyes.





	Pleasant Surprises

**Author's Note:**

> There is such a lack of shadowgast content and that is super sad, so I've decided to start writing/drawing some! Essek seems 100% like a pillow prince and he's valid for that, so let's expect some more of that in the future. As always thank you so much for reading, I hope you enjoy!

Essek liked to watch Caleb, he liked to study him. He liked the way Caleb’s bony fingers rhythmically thrummed against the dark purple wood of his desk, how in his other hand he thumbed through the pages in the book Essek had lent him. How he shook his leg ever so gently while he read, and paused if he reached a point that required extra attention. Essek liked the way that Caleb’s brows furrowed as he read something for the first time, and raised as he started to understand it. 

Caleb’s current book of choice was a thesis paper on the theoretical possibility of using Dunamancy to control time and space on an even larger scale than consecution. Of course, all things discussed in the essay were hypothetical scenarios by scholars who have studied and practiced Dunamancy for centuries; Essek wasn’t too worried about letting the human from the Empire look it over. 

Essek didn’t focus on the possibility of Caleb using this knowledge against the Dynasty, he instead kept his attention on looking over the other wizard. He watched Caleb’s eyes scan the paper, quickly at first and then slowly as he re-read it, soaking in as much information as he could. Essek’s gaze lingered on Caleb’s pale blue eyes for a while before he trailed down to his throat, exposed under the loosened shirt collar. He absentmindedly tugged at his own collar as he watched Caleb swallow, adam’s apple bobbing. 

He imagined how pretty Caleb would look on his knees underneath Essek’s desk, with his cock going down Caleb’s throat. 

It occurred to him, vaguely, that someone was saying something. He blinked a few times and looked up from Caleb’s throat back to his face, and was greeted with a knowing smirk. “Am I boring you, Thelyss?” he asked, cheeks a little rosy from the heat of the candles that melted beside him, droplets of wax spilling onto the desk.

“You could never bore me, Widogast.” Essek grinned and straightened himself out. He had lost the robe and mantle hours before, it hung elegantly off to the side of the room, and his tunic was unfastened at the top. “I was merely admiring you.”

Caleb scoffed, “You have far better things to admire, I’m sure. Far more attractive things that are worth something.” he turned the page, his index finger traced over arcane symbols scrawled on the paper. 

Essek hummed and indifferent noise and leaned onto his elbow on the desk, propping his head in his hand to get a good view of Caleb’s face. “Life isn’t always about the most pretty or valuable things.” he pushed his bottom lip out and batted his pretty eyes at Caleb, watching him to gauge his reaction, “Sometimes, it’s just about what you want in the moment.” 

Wondrously, Caleb almost smiled. The edges of his lips curled up, and his cheeks and the tips of his little round ears flushed the most lovely shade of rose. He carefully set the book down on the desk, closing it with utmost delicacy, and pushed it away. “You’ll have to forgive me but I do find that a bit surprising coming from you, Essek.” Caleb’s voice was smooth, and Essek felt that he could listen to him talk all day. 

“Do you take me for being that shallow?” Essek feigned offense, of course Caleb would think that of him. 

Caleb shifted uncomfortably, “That’s not what I meant, I just…” he sighed and leaned back in his chair, “You’re just so much more impressive than I am, it is just hard to think that somebody like you could be at all,” he paused, “interested in somebody like me.”

“Oh I’m interested in all kinds of things, especially humans who walk into the throne room at the heart of the Dynasty and present the Queen with our Beacon.” Essek said, leaning in towards the other wizard. He stopped a few inches from his face, his eyes a piercing lavender against his grey skin. “The question now, Widogast, is are you interested in somebody like me?” 

Essek watched as Caleb’s eyes lingered on his own body, from Essek’s hands to his throat until they finally met his gaze. “Oh, Essek, I assure you I am very interested in drow who are willing to teach humans from the Empire their most sacred form of magic.”

Much to Essek’s surprise, and delight, Caleb closed the gap between them and kissed him. It was hot and heavy and Essek just melted into it. His eyes closed and he felt a little jolt of adrenaline as Caleb’s hands moved to his waist and pulled him closer. Essek moved with him, allowing himself to straddle Caleb’s lap. 

Caleb ran his hands down Essek’s body until they settled on the under-side of his thighs, holding him tightly. Essek cradled Caleb’s face with his hands as he kissed him, Caleb’s mouth was warm and wet and Essek savored every moment of it. He moved his hands down to Caleb’s torso, resting them on his collarbone. Caleb moved to grab Essek’s ass and the drow smiled into the kiss, “I didn’t think you would be so handsy.” he said. 

Caleb released Essek like his skin was on fire and his eyes shot open, “Oh my, I’m so sorry I should have asked-” 

“ _ Caleb _ ,” Essek huffed, “I don’t want you to stop, you just seem so shy and reserved, I’m pleasantly surprised.” he pressed a kiss against Caleb’s neck and rolled his hips. Caleb let out a soft groan and put his hands back on Essek.

Essek found himself unnecessarily hard in his trousers and found pride in the fact that Caleb was too. They spent the next twenty or so minutes just kissing and touching. Essek left a fair amount of bruises and bite marks on Caleb’s throat which Caleb was certain he’d regret in his post-orgasm state but until then he didn’t  _ care _ what Essek did to him. 

All Caleb cared about was the heat against his skin, everywhere Essek touched felt like an electric shock. “Essek, would you be amenable to the prospect of continuing this with less clothing?” Caleb asked while he peppered light kisses against Essek’s neck. He rocked his hips, grinding against Caleb’s cock at an agonizingly slow pace. 

“I was beginning to think you’d never ask.” Essek reluctantly pulled away from Caleb to strip out of his tunic, tossing it over the desk. Caleb followed suit and let his shirt fall to the floor while Essek stood up and pulled his pants off. There was really no way to get undressed that was  _ actually _ attractive, and the two wizards gave up at making any attempt. Caleb shimmied out of his trousers, kicking them off to one ankle.

“Do you have any slick?” Essek traced a few arcane symbols in the air and when he intertwined his fingers with Caleb’s his palm was wet with oil. “Efficient.” Caleb noted and pulled Essek back onto his lap, hand moving under the curve of his ass as Essek straddled him.

“I’m surprised you don’t know that spell.” Essek kissed Caleb’s jaw, “I could teach you if you want.”

“That would be very useful for, ah, future endeavors?” Caleb half-asked, holding out hope that this wouldn’t be a one time thing. He ran a slicked finger along Essek’s ass before pressing it into him, one knuckle at a time. 

“Well, you’ll have to pay very close attention.” he splayed his palm flat against Caleb’s chest, then started tracing the same pattern he traced in the air onto his skin. Caleb pushed in a second finger, going slower now. He focused on the movement on his torso, visualizing it as Essek moved. The shapes of the spell felt much more angular against his skin, Essek’s fingers snapped into position and Caleb felt entranced in so many ways. As his two fingers reached their end he felt Essek’s warm hand around his cock, slicking it up with the lube from the completed spell. “Can you do it or do you need another demonstration?”

Caleb whined, resisting the urge to thrust into Essek’s hand and finish right then, because that would just be  _ embarrassing _ . Instead he spread his fingers apart and twisted them, making Essek’s hips buckle a bit. “I think I can do it.” Caleb said and started to slide his fingers out, a dazed smile on his lips. It  _ was _ his casting hand, after all. 

Essek frowned and pushed back down onto them, palm going flat against Caleb again. “On second thought, I think you need another lesson.” he started tracing the spell again, slower this time, as his other hand worked on Caleb’s cock. Caleb focused more intently on the sigils this time, needing desperately to memorize it, and added a third finger to Essek’s hole. 

Having Essek spread open on his lap was something Caleb had imagined before, on desperate nights alone in the Xhorhouse, but nothing could have prepared him for the real thing. He was captivating, the high points of his skin flushed a lavender color and a genuine smile on Essek’s face. It was more than Caleb could have ever dreamed of. Essek almost faltered in his spell as Caleb finally pushed all the way to the knuckle, his casting fingers twitched during the spell but ultimately remained accurate. 

Essek finished the arcane sigil, and brought the slick down to Caleb’s cock. He pumped his hands while Caleb worked him open. “I think I can cast it now.” Caleb said in a rushed voice as he pulled his fingers out of Essek, earning a disappointed sigh from the other wizard. 

“You are a quick learner.” Essek lifted his hips up and positioned himself over Caleb’s cock, waiting. Caleb mimicked to the best of his ability the spell that Essek had traced over his body, with shaky fingers and a mind distracted by the burning heat in his groin he somehow managed to pull it off. He grinned to himself as he felt the arcane oil spread across his fingers; be dragged the slick over Essek’s crack and then rubbed the rest of it on his cock.

Essek waited, pressing hot kisses against Caleb’s skin while he pushed in. Caleb was everything Essek had hoped he would be and more, he felt his own cock twitch as he sank all the way to Caleb’s hilt. His face was buried in the crook of Essek’s neck, leaving light kisses and bruises in his wake. 

Caleb stopped going slow and rocked his hips as quickly as he could from a wooden chair. With one lucky thrust he found Essek’s prostate and Essek toppled onto Caleb’s shoulders, “Ooh, fuck,  _ Caleb _ .”

Caleb’s hands moved all across Essek’s body, trying to touch as much as he could all at once because  _ fuck, _ Essek felt so  _ nice _ , and Caleb didn’t deserve to have nice things but he wasn’t going to deny himself this. He snapped his hips up again, trying his best to hit that spot for Essek; to be good for Essek. So that maybe, gods willing, he would want to do this again. (Or at the very least he wouldn’t stop all contact with him entirely after this encounter) 

Essek was speaking in a language that Caleb didn’t understand, presumably Undercommon. It was noticeably different than most languages Caleb was used to, shorter and harsher words and accents, but all of Essek’s rambling went straight to Caleb’s dick. He moaned and bit down at the junction between Essek’s neck and shoulder, making Essek groan. 

The wizard rocked his hips forward, trying to get some friction on his untouched cock. Essek’s fingers were digging into Caleb’s shoulders, his perfectly manicured nails leaving thin scratches on Caleb’s freckled skin. 

“I’m afraid I won’t last much longer,” Caleb said in a rush, pressing down on Essek’s hips. “you should probably get off soon.” 

Essek sank down on Caleb and shook his head, “I want you to finish inside of me, Widogast.” he said and bounced on Caleb’s cock, “That way when I’m fucking myself tonight I can use you as my slick.” 

Caleb whined as Essek spoke, imagining the drow sprawled out on his canopy bed with a toy in his ass moaning his name. The thought and Essek’s words were enough to push Caleb over the edge, his hand messily jerking Essek’s cock as he spilled inside of him up. The feeling of Caleb’s cum filling him up while Caleb twisted and pulled on his cock with frantic elegance had Essek moaning and cursing in a language unfamiliar to Caleb as he came across Caleb’s chest. 

Essek leaned forward and rested his forehead against Caleb’s shoulder, arms finding purchase around Caleb’s neck. Caleb’s hands traced the edge of Essek’s body, eventually settling on his hips. Essek lazily lifted one hand in the air, fingers snapping into place as he traced symbols. As the spell came to a close a glass object materialized in Essek’s hand. He regretfully pulled back from Caleb and lifted himself off of the wizard, moving an arm behind himself to push the object inside. 

“Oh, fuck, you were serious.” Caleb’s cheeks flushed an even deeper pink.

Essek’s lips curled into a smile as he grabbed Caleb by the cheeks and pressed a slow kiss to his lips. His post-orgasm brain was coming back to him and would surely be embarrassed about this later, but his sex-brain didn’t care in the slightest. Caleb kissed him back, hands lingering on Essek’s body like he was scared of letting go. 

“I assure you, Caleb, I am  _ always _ serious.” he said.

Caleb waved his hand across his stomach, tracing a brief spell into the air, and the cum and sweat disappeared off of his body. “Want a clean up?” he offered, Essek nodded. 

Not a second too soon a knock came to the door. “What is it?” Essek asked, putting on his best work-voice. 

“There are some, um, people here to see you, Sir.” came the voice of a servant. “A young tiefling woman is insisting that she is your friend.” 

Essek and Caleb both sighed, “Tell them that Mister Widogast will be returning to them shortly.” 

“Right, Sir.” footsteps disappeared down the hall and Caleb flashed an apologetic smile. 

“I’m sorry about my friends.”

Essek waved a hand dismissively, “Do not worry about it,” he said and removed himself from Caleb’s lap. “I suppose I should be getting back to work. Prisoners to interrogate, magic to study.” he said and started gathering his clothes. 

Caleb followed suit, retying his pants and tucking his tunic in. “Yes, magic to study and monsters to fight.” he smiled awkwardly as he finished dressing. 

“We can revisit this book next time.” Essek said finally as they both finished making themselves look presentable again. “And maybe revisit other aspects from today?” 

Caleb nodded a little too quickly, “Ja, that would be very nice.” he said. 

“Wonderful!” Essek smiled as he pulled his mantle back into place, “Well, until next time, Caleb.” he smiled and Caleb nodded. 

“Until next time.” he left Essek’s study and let himself out of the house, meeting his friends outside in the street. 

“That took a  _ long _ time.” Jester said, “Were you guys pooping?” 

“Or making out.” Beau pointed to the side of Caleb’s neck, a light bruise was starting to form. Caleb’s hand shot up to the side of his neck and covered it, “Definitely making out.” 

“Oh my gosh,  _ Caleb _ .” Jester ran up to him, eyes wide, “Why didn’t you tell us you were going on a date? We wouldn’t have come to disturb you for at least another three hours. Oh my gosh, was it like that part in Tusk Love where Oskar and Guinevere went to the library to get information on her past but then they ended up having lots of sex against all of the books?” 

Caleb’s face was beat red, as was Fjord’s. “Oh my god, you two nerds would have a fucking thing for libraries.” Beau said and groaned. 

“I’ll kill him if he ever hurts you, Caleb, but I have to admit he seems like a very nice boy.” she shrugged, “You could do worse.” 

It was almost like Caleb forgot how to talk, because he just stared at the ground with his hands around his neck. 

“Come on, guys, leave Caleb alone.” Caduceus ushered the gang to start walking back to the Xhorhouse. “He’s allowed some privacy, just like we all are.” 

“Fine, fine.” Jester said and kept walking, biting the inside of her cheek. “Oh my Gosh, Caleb, you’re like living that smut book we read so long ago! The courting book!” 

“Ah, the one with the racial slur in the title?” Beau asked. 

“Just the one! We should really rewrite that book.” Jester tapped her chin, “Maybe ‘ _ Doing the Drow _ ’ instead?” 

Beau barked out a laugh, “That’s pretty good, to be honest.” 

“I thought so too.” Jester smiled proudly while Caleb shrunk farther inside of his tunic. “I’m sorry, Caleb, I’ll stop teasing you today. I’ll wait until next time.” 

“Ja, okay.” Caleb mumbled.


End file.
